CA1295072C - Microbiocidal compositions comprising an aryl alkanol and a microbiocidalcompound dissolved therein - Google Patents

Abstract

ABSTRACT OF THE DISCLOSURE

Liquid microbiocidal solutions are disclosed containing an aryl alkanol and a microbiocidal compound dissolved in the aryl alkanol. By adding the liquid microbiocidal solution to a polymer composition, microbiocidal properties are imparted to the polymer.

Description

5(:J 72 MICROBIOCIDAL COMPOSITIONS COMPRISIN~ AN ARYL ALKANOL
AND A MICROBIOCIDAL COMPOUND DISSOLVED THEREIN
.

BACKGROUND OF THE INVENTION

1. Field of the Invention This invention relates to liquid microbiocidal solutions containing an aryl alkanol and a microbiocidal compound dissolved in said aryl alkanol.
This invention also relates to compositions comprising a polymer processing aid and a microbiocidal compound dissolved in an aryl alkanol.
The present invention further relates to a process for imparting microbiocidal properties to polymer compositions comprising adding to the polymer composition a li~uid microbiocidal solution comprising an aryl alkanol and a microbiocidal compound dissolved therein.
This invention also relates to a process ~or imparting microbiocidal properties to a polymer composition comprising adding to the polymer composition a composition comprising a polymer processing aid and a microbiocidal compound which is present in the polymer processing aid as the solute in an aryl alkanol solvent.
This invention further relates to compositions comprising a solution of a liquid plasticizer for vinyl resins and a micro-biocidal amount of a microbiocidal compound dissolved in an aryl alkanol.
This invention further relates to vinyl resin compositions comprising an admixture of a vinyl resin and a vinyl resin plasticizer containing, in an amount su~ficient to impart microbiocidal properties to the vinyl resin composition, a microbiocidal compound dissolved in an aryl alkanol.
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2. Prior ~rt It is presently common practice to protect polymer or plastic compositions from microbial, e.g. bacterial or fungal, attack by incorpora~ing a microbiocidal composition into the pol~mer or plastic. The resulting polymer compositions prevent the de-terioration of articles formed from the polymer compositions due to microbiological attack on the plas~ici~ers or other polymer additives which are normally incorporated into the polymer to .~

129~2 impart desirable phys.ical properties to the article and to facilitate forming of the article.
Many of the available microbiocidal materials are solid and, in order to incorporate them homogeneously in the polymer composition, it is ~ecescary to first mix them with a liquid which solubilizes or disperses the material unifor~ly and thereaf~er, mix the thus-formed li~uid composition with the polymer.
Unfortunately, the solubility of many of the microbiologically active materials in the more common solvent materials is quite low. Therefore, it is either difficult to incorporate a sufficiently high concentration of the microbiocidal material with the polymer or, if sufficiently high concentrations of the microbiocidal material can be incorporated in the polymer, an undesirably high concentration of the solvent m~st also be incorporated in the polymer with the resultant deterioration of the desirable characteristics of the polymer composition.
Attempts to solve these problems have met with varying, often limited, success. For example, U.S. Patent No. 3,288,674 issued November 29, 1966 to Yeager and U.S. Patent No. 3,689,449 issued September 5, 1972 to Yeager and Wilson disclose the use of solvents having a labile hydrogen, preferably nonyl phenol, to dissolve microbiocidally ac~ive phenoxarsine compounds, the resulting solutivn being subsequently incorporated into resin compositions, Unfortunately, the solubility of the phenoxarsine m nonyl Fhenol plasticizer formulations is 1 ~ ted to low concentrations which necessitates incorporating nonyl phenol in the resin at higher concentrations than desirable in order to attain the desired phenoxarsine levels in the resin.
U.S. Patent No. 3,360,431 issued December 1967 to Yeager discloses the use of labile hydrogen-containing solvents, preferably nonyl phenol, to dis~olve microbiocidally active arsenobenzene compounds for subsequent addition to resin compositions.
U.S. Patent No. 4,049,822 issued September 20, 1977 to Rei and Wilson discloses microbiocidal phenoxarsines dissolved in glycyl phosphites or glycyl phosphonates, the resulting solution being subsequently incorporated into resin compositions~

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In accordance with the present invention there are provided liquid microbiocidal solutions comprising an aryl alkanol and a microbiocidal compound dissolved therein said microbiocidal compound being selected from the group consisting of N-(2-methylnaphthyl) maleimide, ~LZ~ 7;~

isoindole dicarboximides having a sulfur atom bonded to the nitrogen atom of the dicarboximide group, isothiazolinone compounds, phenoxarsines and phenarsazines.
Also provided in accordance with this invention are compositions comprising a plasticizer as a polymer processing aid and, in an amount at least sufficient to impart microbiocidal properties to the composition, a microbiocidal compound which is present in the composition as the solute in an aryl alkanol solvent, said microbiocidal compound being selected from the group consisting o~ N-(2-methylnaphthyl) maleimide, isoindole dicarboxamides having a sulfur atom bonded to the nitrogen atom of the dicarboximide group, isothiazolinone compounds, phenoxarsines and phenarsazines.
There is also provided in accordance with the present invention a process or imparting microbiocidal properties to a polymer composition comprising adding~to the polymer composition a liquid microbiocidal solution comprising an aryl alkanol and, in an amount sufficient to impart microbiocidal properties to the polymer composition, a microbiocidal compound dissolved in the aryl alkanol, the microbiocidal compound being selected from the group consisting of N-(2-methylnaphthyl) maleimide, isoindole dicarboximides having a sulfur atom bonded to the nitrogen atom of the dicarboximide group, isothiazolinone compounds, phenoxarsines and phenarsazines. This invention also includes the product produced by this process.
There is still further provided in accordance with this invention a process for imparting microbiocidal properties to a polymer composition comprising adding to the polymer composition a composition comprising a polymer processing aid and, in an amount at least sufficient to impart microbiocidal properties to the polymer composition, a microbiocidal compound which is present in the polymer processing aid as the solute in an aryl alkanol solvent, the microbiocidal compound selected from the group consisting of N-(2-methylnaphthyl) maleimide, isoindole dicarboximides having a sulfur atom bonded to the nitrogen atom of the dicarboximide group, isothiazolinone compounds, phenoxarsines and phenarsazines. The product of this process is also included in the invention.

DESCRIPTION OF THE PR~FERRED EMBODIMENTS

The aryl alkanols useful as solvents in the practice of this invention are compounds which have an hydroxyl group attached to an aromatic ring through an alkylene group. That is, the aryl alkanols of this invention contain an aromatic ring to which is attached a group having the formula -R-OH where R is a straight or branched-chain alkylene group, preferably having 1-6 carbon atoms, more preferably 1-3 carbon atoms and most preferably 1 carbon 3a atom. ~he alkylene group may be unsubstituted or substituted with other groups such as, for example, halogens, amines, methyl, hydroxyl, or alkoxyl groups.
~ he term aryl as used herein refers to aromatic rings which may be substituted with functional groups. Ex~mples of such aromatic rings include, but are not limitecl to, benzene, na-phthalene, and biphenyl rings. When the aryl group is substituted with functional groups r it may have any nun~er of groups attached to the aromatic ring, it being required only that the type of functional groups, their position on the ring and/or their number does not interfere with the aryl alkanol'~ ability to dissolve the microbiocidal compound or, if it is to be employed as part of a polymer composition, its compatibility with the polymer. Ex-amples of such functional groups on the aryl rings include, but are not limi~ed to, halogen, aryloxy, amino, hydroxyl, alkoxyl, and nitro groups.
The aryl alkanols useful in the practice of this invention may be further defined by the following general formula:

OH
R

wherein A is an aromatic ring, pxeferably benzene, which may be unsubstituted, e.g. phenyl, or substituted with one or more halo, aryloxy, amino, hydroxyl, alkoxyl or nitro groups; and R is a straight or branched chain alkylene group, preferably having 1-6 carbon atoms, which may be unsubstituted or substituted with halo, amino, methyl, hydroxyl or alkoxyl groups.
The aryl alkanols which are useful in the practice of the present invention are those in which the hydroxyl group of the alkanol is a primary, secondary or tertiary alcohol. The preferred aryl alkanols are those in which the hydroxy group is a primary alcohol.
Examples of ary} alcohols which may be employed in accordance with this invention include, but are not limited to, the following:

~295C:1 72 OH

benzyl alcohol OH
CH -C-H

styralyl alcohol (methyl benzyl alcoholl phenethyl alcohol HO-CH2-CH2-CH2~

3-phenyl-1-propanol OH
: ~cl 2, 4-dichlorobenzyl alcohol OH
CH

0~

:
::
:
: m-phenoxy benzyl alcohol Of these aryl alkanols, benzyl alcohol, 2, 4-dichlorobenæyl alcohol, and styralyl alcohol are preferred, benzyl alcohol being especially preferred.
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The aryl alkanols exemplified above are all liquids with the exception of 2,4-dichlorobenzyl alcohol, which is a solid. This compound has quite surprisingly been found to act as a solvent (or co-solvent) for those microbiocidal compounds which are liquids.
If the 2,4-dichlorobenzyl alcohol is heated slightly it melts and then can be combined with the liquid microbiocidal compound to form a stable solution. The 2,4-dichlorobenzyl alcohol also exhibits microbiocidal activity by itself. Thus, it can be dissolved in another aryl alkanol, for example benzyl alcohol, to produce a microbiocidal solution in accordance with this invention.
A wide variety of microbiocidal compounds are useful in the practice of this invention. In general, the useful microbiocidal compounds possess microbiocidal activity and are soluble in an aryl alkanol. If the aryl alkanol/microbiocidal compound solution is to be employed in compositions containing polymer processing aids and/or polymers, the microbiocidal compound should be compatible with such processing aids or polymers.
Examples of the types of microbiocidal compounds which may be employed in this invention include, but are not limited to, phenoxarsines(including bisphenoxarsines), phenarsazineY
(including bisphenarsazines), maleimides, isoindole dicarboximides, having a sulfur atom bonded to the nitrogen atom of the dicarboximide group, halogenated aryl alkanols and isothiazolinone compounds.
The microbiocidal phenoxarsine and phenarsazine compounds useful in the compositions of this invention include compounds represented by the formulas:

` A5 ~
X and A
Y
.1 ~ As~

~2~SID7~
where X is halogen or thiocyanate, Y is oxygen or sulfur, Z is oxygen or nitrogen, R is halo or lower alkyl, and n is O to 3.
Examples of these phenoxarsines and phenarsazines include, but are not limited to, 10-chlorophenoxarsine; 10-iodophenoxarsine;
10-bromophenoxarsine; 4-methyl-10-chlorophenoxarsine;
2-tert-butYl-lO~chloroPhenoxarsine; 1, 4-dimethyl-10-chlorophenoxarsine; 2-methyl-8, 10-dichlorophenoxarsine; 1, 3, 10-trichlorophenoxarsine; 2, 6, 10-trichlorophenoxarsine; 1, 2, 4, 10-tetraohlorophenoxarsine; 10, 10'-oxybisphenoxarsine (O~PA); 10-thiocyanato phenoxarsine; and 10, 10'-thiobisphenoxarsine; 10,10'-oxybisphenarsazine and 10,10'-thiobisphenarsazine~
The microbiocidal maleimide compounds useful in the compositions of this invention are exemplified by a preferred maleimide, N-(2-methylnaphthyl) maleimide.
The microbiocidal compounds useful in the practice of this invention which are isoindole dicarboximides having a sulfur atom bonded to the nitrogen atom of the dicarboximide group are compounds which contain at least one group having the structure:

f ~ N-S-~C~
o The preferred isoindole dicarboximides are the following:

f~ c~ c~ cl ! N-S-C-CH
~/ ~~C~ Cl\CI
O

bis-N-[(l, 1, 2, 2-tetrachloroethyl)thio]-4-cyclohexene-1, 2-dicarboximide o N-S-C-C
C Cl O
-N-trichloromethy}thio-4-cyclohexene-1, 2-dicarboximide - -- .; 7 , ~95~2 ~ N-S-C-C\
o N-trichloromethylthio phthalimide The halogenated aryl alkanols which can be used as microbiocidal compounds in accordance with this invention are exemplified by a preferred compound, 2, 4-dichlorobenzyl alcohol.
An example of a preferred isothiazolinone compound useful in the composition of this invention is 2-(n-octyl-4-isothiazolin-3-one).
The most preferred microbiocidal compounds are the bisphenoxarsines and bisphenarsazines having the formula:

[~As~

[~s~

where Y is oxygen or sulfur and Z is oxygen or nitrogen. Of these bisphenoxarsines and bisphenarsazines, the most preferred are 10, 10'-oxybisphenoxarsine; 10, 10'-thiobisphenoxarsine; 10, 10'-oxybisphenarsazine; and 10, l~'-thiobisphenarsazine.

The microbiocidal compositions useful in this invention should be employed in an amount at least sufficient to impart micro-biocidal properties to the composition or material containing them. Thi~ amount can vary widely depending upon the particular microbiocidal compound employed, the other components of the composition in which i~ is employed, the environment in which it will functio~ and several other factors. The minimum amount of microbiocidal compound employed will be determined by what is known in ~he art as its Minimum Inhibitory Concentration (MIC).
The maximum amount of microbiocidal compound which can be employed is determined only by the amount of microbiocidal compound which can he uniformly incorpora~ed into a particular composit:ion without adversely af~ecting the physicaL proper~ies of the composition.
In general, the compositions of this invention which possess ~2~35~72 microbiocidal properties contain from about 50 parts per million (ppm) to about lO,OOO ppm, preferably about lOO ppm to 500 ppm, of microbiocidal compound.
The liquid microbiocidal solutions of this invention preferably contain much more microbiocidal compound than would be necessary simply to impart the desired microbiocidal properties to them. This is also true for the polymer processing aid-containing composition. These compositions can contain large amounts of microbiocidal compound since they are adva~tageously employed as "concentrates" to produce composltions which have a lower concentration of microbiocidal compound, but still have the desired degree of microbiocidal activity. For example, the liquid microbiocidal solutions may contain from about 0.1 to about 30 weight percent microbiocidal compound ~based on total solution weight). However, a solution containing, for example, 25%
microbiocidal compound may be used to prepare a polymer processing aid-containing composition which contains only about 5%
microbiocidal compound, which polymer proceQsing aid-containing composition may in turn be used to prepare a polymer composition containing only lOO to 500 ppm microbiocidal compouncl.
The microbiocidal solutions of this invention may be employed as additives for polymer compositions to impart microbiocidal properties to said polymer~compositions. They may be added either directly to the polymer composition or they may be first incorporated into a polymer processing aid which serves as a carrier for incorporating the microbiocidal solutions into the polymer composition. When the latter manner is chosen, the polymer processing aids may be any of a variety of materials which are compatible with the polymer composition and microbiocidal solution (e.g. the microbiocidal compound does not precipitate or otherwise sepaxate from the composition solution when used with the proce~sing aid). Examples of these polymer processing aids include, but are not limited to, plasticizers, lubricants, and volatile a~d non-volatile solvents. Specific examples of these processing aids include, but are not limited to, typical plasticizers such as tricresyl phosphate, dipropylene glycol dibenzoate, diphenylcresyl phosphate, dipropylene glycol dibenzoa~e, diphenylcresyl phosphate, epoxidized soya ~ ~ oil, epoxidized tallate, dioctyl azelate, di(2-ethyl hexyl1 phthalate, alkyl aryl phosphates,diisobutyl phthalate, diisodecyl phthalate, hydrogenated me~hyl rosin es~er, n-octyl n-de yl phthalate, mixed n-alkyl phthala~es, butyl benzyl ph~halate, di-n-octyl phthalate, di-n-decyl phthalate, 3,4-epoxycyclohexyl methyl 3,4-epoxycyclohexane carboxylate, trioctyl trimelli~ate and low molecular weight polymeric plasticizers such as~Paraplex G-3ollplasticizer sold by Rohm ~ ~Iaas *- ~rade Mark :, Co. and the like. Of these plasticiæers, di(2-ethyl hexyl) phthalate, diisodecyl phthalate, butyl benzyl phthalate and epoxidized soyab ~ oil are preferred. Other polymer processing aids useful in this invention include, but are not limited to, polypropylene glycol;
1,4-butanediol; silicone oils such as polydimethylsiloxane; and methyl ethyl ketone.
As previously indicated, the concentration of microbiocidal compound in the microbiocidal solution may be sufficiently high that the polymer processing aid-containing composition prepared from said microbiocidal solution will'in turn contain enough micro biocidal compound that, when the polymer processing aid-containing composition is added to a polymer, the ultimately-formed polymer composition and articles prepared therefrom will have microbiocidal properties. It is in this aspect of the invention where the solvents employed in the practice of the present invention are particularly advantageous.
The aryl alkanols of this invention are capable of forming microbiocidal solutions which will produce polymer processing aid-containing compositions containing concentrations of microbiocidal compounds significantly higher than could be achieved with prior art solvents. For example, heretofore OBPA-containing plasticizing compositions contained a maximum of about 2~ by weight OBPA based on the weight of the plasticizing composition~ It has now been qui~e unexpectedly found that the aryl alkanols of this invention are capable of producing OBPA-containing plasticizing compositions containing at least 5%
by weight OBPA based on the weight of the plasticizing composition.
This unexpected ability of the aryl alkanols to produce polymer processing aid-containing compositions containing high levels of microbiocidal compound leads to several very significant advantages. For example, shipping and handling cost savings are achieved because more "active ingredient" (the microbiocidal compound) can now be dissolved in a given amount of polymer processing aid-containing composition. Stated another way, for a given amount of microbiocidal compound, less "inert ingredients"
(solvent and polymer processing aid) are required to produce a polymer processing aid-containing composition, resulting in raw material cost savings. Also, because less inert ingredients are needed, handling and shipping costs are lowerO
The polymex processing aid-containing compositions of this invention also minimize the potential ef~ects of the solvent for the microbiocidal compounds on polymer formulations containing them. Because les~ solvent is required to prepare a polymer proc~ssing aid-containing composition containing a given level of ., microbiocidal compound, less solvent is introduced into the polymer formulation. Therefore, if the solvent is not entirely compatible with the other components of the polymer formulation, the negative effects of that incompatibility will be minimized.
Apart from their ability to dissolve more microbiocidal compound, the aryl alkanols of this invention also have the surprising advantage of producing polymer processing aid-con-taining compositions which are low in odor and less irritating compared to the solvents disclosed in the prior art such as nonyl phenol and phosphites.
It has also been quite surprisingly discovered that the microbiocidal solutions of the present invention can often be prepared at temperatures considerably lower than those re~uired with the solvents of the prior art. For example, in order for nonyl phenol to dissolve O~PA, a nonyl phenol/OBPA mixture must generally be heated to about 300F. However, a benzyl alcoholtOBPA solution according to the present invention may be prepared by heating to only about 140F. Obviously, when large masses of material are required to be heated, as in a commercial operation, the lower temperature requirement of the microbiocidal solutions of this invention can result in tremendous energy savings. The lower temperature also helps prevent undesirable chemical reactions (such as the oxidation of benzyl alcohol to benzaldehyde) from occurring.
The polymers employed in the processes and products of this invention cover a wide variety of materials. In general, they include thermoplastic and thermosetting polyn~ers, elastomers and other materials commonly known as "plastics". Other organic materials, for instance naturally occurring materials such as natural rubbers, cellulose and the like are considered full equivalents of the "polymers" of this invention and should be included within that term. Examples of the polymers useful in the practice of this invention include, but are not limited to vinyl resins ~such as those made from vinyl chloride and/or vinyl esters) polyolefins (such as polyethylene and polypropylene), elastomeric polyurethanes, nylon, polys~yrene, polyesters (such as polyethylene terephthalate), polycarbonates, acrylonitrile-butadiene-styrene (ABS~ copolymers, SBR rubbexs, styrene-acrylonitrile copolymers, acrylic polymers, thermosetting polyurethanes (such as those used for foams and coatings), phenolic resins, silicone rubbers, natural rubber, EDPM polymers, cellulose and its derivatives, epoxy resins and variou~ latexes.
The microbiocidal solutions of this invention can be prepared by simply adding the desired amount of microbiocidal compound to the aryl alkanol solvent, heating the resulting mixture to a ~295 Oi~Z
temperature which will cause the microbiocidal compound to dissolve, and maintaining that temperature until all of the microbiocidal compound dis olves. The resulting solution can then be cooled to room temperature. In this manner, stable microbiocidal solutions, i.e. those wherein no significant amount of micro~iocidal compound precipitates from the solution upon cooling to room temperature, can be formed containing up to about 30% by weight microbiocidaL compound based on the weight of the resulting microbiocidal solution.
The polymer processing aid-containin~ compositions of the present invention may be prepared by merely adding the polymer processing aid to a microbiocidal solution prepared as described above and mixing at room temperature until a uniform solution results. Alternatively, all ingredients of the polymer processing aid-containing composition (microbiocidal compound, aryl alkanol and polymer processing aid) can be mixed together and heated until the microbiocidal compound dissolves.
The microbiocidal solutions of this invention can be used to impart microbiocidal properties to polymer compositions. This can be done by simply adding the microbiocidal solution, either alone or as part of a polymer processing aid-containing composition, to the polymer composition by any of several convenient methods known in the art. Thus, for instance, the polymer composition can be melted and the microbiocidal solution or polymer processin~
aid-containing composition added to and mixed with lt (as in an extruder). Alternatively, the polymer can be softened with or dissolved in a solvent and the microbiocidal solution or polymer processing aid-containing composition added to and mixed therewith.
The compositions of this invention will now be further described by reference to several embodiments thereof which are summarized in the following Table A. In these embodiments, al~
percentages are by weight based on the total weight of the composition. Also, for the purposes of Table A, the microbioci-dal compounds have been divided into two classes designa~ed "OBPA"
and "non-OBPA". "OBPA" refers to the phenoxarsine and phenarsazine compounds described elsewhere herein which are pre~erred in the practice of this invention. The terms "non-OBPAi' refers to all other microbiocidal compounds which are useful in the invention~

~' -5(~72 TABLE A

Microbiocidal Cmpd. Amount of Polymer Wt ratio of dissolved in MicrobiocidalProcessing aryl alkanol/
aryl alkanol Compound Aid microb. cmpd.
OBPA Microbiocidal amnt. - -non-OBPA Microbiocidal amnt.
OBPA 0~1 - 30%
OBPA 25 - 30%
OBPA 25~ - -non-OBPA 0.1 - 30~ - -OBPA Microbiocidal amnt. Plasticizer OBPA Microbiocidal amnt. do 0.5/1-5/1 OBP~ Microbiocidal amnt. do 0.5/1-3/1 OBPA Microbiocidal amnt. do 1~1-3/1 OBPA 1-5~ do 0.5/1-5/1 OBPA ~2% do OBPA ~2~ do 0.5/1-5/1 OBPA ~5~ do 0.5/1-5/1 OBPA 2% do 4/1 OBPA 2~ do 3/1 OBPA 2~ do 1/1 OBPA 5~ do 4/1 OBPA 5~ do 3/1 OBPA 1% do 4/1 OBPA 1~ do 3/1 OBPA 1% do 1/1 OBPA 5-204 do 3/1-5/1 non-OBPA Microbiocidal amnt. do non-OBPA Microbiocidal amnt. do 0.5/1-5/1 non-OBPA Microbiocidal amnt. do 0.5/1-3/1 non-OBPA Microbiocidal amnt. do 1/1-3/1 non-OBPA ~2~ do non-OBPA ~2~ do 0.5/1-5Jl non-OBPA ~5~ do 0.5/1-5/1 non-OBPA 5-20% do 3/1-5/1 The ~ollowing examples illustrate the present invention, and are not intended to limit the invention or its scope in any manner. As used in the examples and throughout this specification, all parts and percentages are by weight unless otherwise indicated.

Several microbiocidal solutions were prepared by mixing the microbiocidal compounds and solvents indicated in Table I and heating the resulting mixtures at the temperatures indicated in Table I until they became clear. (The numbers in parentheses indicate the weight percent of each ingredient based on solution weight). The resulting clear solutions were then cooled to room temperature and aged at room temperature (RT~ for varying periods of time, after which they were examined to determine whether the microbiocidal compound was still in solution.

.
Polymer processing aid-containing compositions were prepared by first preparing a solution of microbiocidal compound in an aryl alkanol solvent as described in the foregoing examples, blending the thus-formed solution with a polymer processing aid and heating the blend while stirring until thoroughly mixed. Several polymer processing aid-containing compositions were prepared in this manner using the ingredients and conditions indicated in Table II
with the results also indicated in Table II. All percentages in Table II are by weight percent based on the total weight of the compositions.

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~2~5ai'~ 2 EXAMPLE_3 Several of the compositions shown in Table I and Table II were subjected to a~ing ~storage stability) tests by aging the sample at room temperature for seven days, after which they were subjected to five freeze-thaw cycles. Each freeze-thaw (F-T) cycle consisted of storing the sample in a freezer at 0F for two days followed by one day at room temperature. After five of these cycles the samples were examined for stability with the following results:

TABLE III

Solution or Stability after Stability after Plasticizing Comp'n No. 7 d~ys RT S F-T cycles F Stable Not Stable K Stable Not Stable I Stable Stable J Stable Stable 58 thru 78 Stable Stable It should be emphasized that those compositions in Table III
which were not stable after the F-T cycles are still quite useful in the practice of this invention. For instance, they can be used to prepare polymer processing aid-containing compositions which are stable after F-T cycles, or can be stored and used under conditions which avoid F-T cycles.
:
Additional stability tests were conducted to determine the effects on solution stàbility when the weight ratio of aryl a}kanol to microbiocidal compound and the type of polymer processing aid is varied. These tests were performed by first preparing a concentrated solution of the microbiocidal compound (OBPA) in the aryl alkanol (benzyl alcohol) by heating a mixture of the two materials to 160F until a clear solu~ion results.
Immediately a~ter preparation of the concentrated solution, a polymer processlng aid-containing solution was prepared by diluting the concentrated aryl alkanol/microbiocidal compound solution with a polymer processing aid at room temperature. The resulting composition was then stored in a glass vial at room ~295~72 temperature and the solution stability was recorded after 24 hours and after 7 days aging. A composition wa~ considered to ~ail after the first signs of microbiocidal compound precipita-tion or liquid phase separation. After 7 days at room tempera-ture, the solutions were subjected to 5 freeze~thaw (F-T) cycles at 0F. A cycle consisted of storing the sample for 2 days in a freezer (at 0F) followed by one day at roo:m temperature. The results of these stability tests are summarized in Table IV
where all percentages are by weight based on total composition weight.

~2~5~2 TABLE IV
Wt. ratio Polymer ~ E3enzyl E3enzyl alc/ Processing Stability2 after 5 F-T
SAMPLE OBPA alc. O~PA Aid (%) 24 hrs. 7 days cycles lA 2% 6% 3Jl ES0(92%) OK OR OK
2A 5~15% 3/1 ESO(80~) OK OK OR
3A 2~ 4% 2/1 ESO(94%) OK OK ~
4A 5~10~ 2/1 ESO(85%) OK OK OK
5A 2~ 2~ 1/l ESO(96%) OK OK OK
6A 5~ 5~ 1/l ESO(9Og~ OR P P
7A 30 9~ 3/l SIL(880) SEP SEP SEP
8A 5~150 3/l SIL~80%) SEP SEP SEP
9A 3g 6~ 2/1 SIL(91~
lOA 5~10~ 2/1 SIL~853) - - ~
11A 3% 3~ 1/1 SIL(94%) _ _ _ 12A 53 5~ 1/1 SI~(90~
13A 2% 6% 3/1 PPG(92%) OK OK OK
14A 5~153 3/1 PPG(80~) OK OK OX
15A 2~ 4% 2/1 PPG~94%) OK OK OK
16A 5~10% 2/1 PPG(85~) OK OK OK
17A 2% 2% 1/1 PPG(96~) OK OK P
18A 5~ Sg l/1 PPG(90~) OK P P
19A 1~ 3% 3/l DOP(96~) OK Ok OK
20A 2~ 6% 3/1 DOP(92~) OK OK OK
21A 5~15% 3/l DOP(80~) OK OK OK
22A 1g 2~ 2/1 DOP(97%) P P P
23A 2% 43 2/1 DOP(94%) OK OK OK
24A 5%104 2/1 DOP(85~) OK OK P
25A ~ 1/1 DoP(98~) OK OK OK

26A 2% 2i 1/l DOP(96~) OK OK OK
27A S~ 5% 1¦1 DOP(90~) OK P P
28A 1~ 3% 3/l DIDP(96~) OK OR OX
29A 2~ 6~ 3/1 DIDP¦92~i OK OK OK
30A 5~15~ 3/1 DIDP(80~) OK OK OK
31A 1~ 2~ 2/1 DIDP(970) OK OK OR
32A 2~ 4~ 2/1 DIDP(94%) P P P

12956~7Z

_ . _ . . . .. . .
TA3LE IV (cont ' d) ~ .. .__ 3 Wt. ratio PoLymer % Benzyl Benzyl alc/ Processing Stability2 after 5 F-T
SAMPLE OBPA alc. 08PA Aid (3~ 24 hrs. 7 day~
33A 5310% 2/1 DIDP(853) P P p 34A 13 l& 1/1 DIDP(983) OR OK OK
35A 23 2& 1/1 DIDP(96%) OK OK OK
36A 53 53 1/1 DIDP(90%~ ~OK OK P
37A 1% 3~ 3/1 ~3Pt963) OK OR OK
38A 23 63 3/1 8BP~923) OK OK OR
39A 5315% 3/1 BBP(803) OK OK OK
40A 13 2% 2/1 BBP(97%) OR OK OR
41A 23 43 2/1 BBP(943) OX OR OR
42A 5&103 2/1 BBP~85~) OX OK OK
43A 13 13 1/1 ~9P~98&) OK OK OK
44A 2~ 2~ 1/1 38P(963) OK OK OK
45A 53 53 1/1 BBP(903) OK OK OK
46A 23 63 3/1 MS(923) OK OK SEP
47A 5%153 3/1 MS(803) OK OK SEP
48A 23 43 2/1 MS(943) OK OK SEP
49A 5~103 2/1 MS(853) OX OK SEP
50A 23 2% l/l MS(963) P P SEP
51A 53 53 1/1 MS(903) P P SEP
52A 23 63 3/1 MEX(923) OK OK OK
53A 5%15% 3/l MEK(803) OK OK OK
54A 23 43 2/1 MEK(94g) OK OK P
: 55A 53103 2/1 MEK(853) OK OK OK
56A 23 2% 1/1 MEK(963) OK OK P
57A 5% 5% l/1 MEX(903) OX OK P
ESO Ls epoxidL~ed sdya bean oil SIL is silicone oil PPG is polypropylene glycol DOP is di~2-ethyl hexyl)phthalate DIDP is diisode~yl phthalate *
8BP is butyl benzyl ph~h~late sold a~Santicizer S-16d'by Mon~anto Industrial Chemicals Co.
MS is mineral spirits MEX i9 methyl ethyl ketone 20~ - solution ls stable p a preclpitat~, solution ha~ ~ailed SEP - liquid - liquid separation * T.rade r~.rk . .

~2~S~72 The data in Table IV demonstrates that a weight ratio of benzyl alcohol to OBPA of about 3/1 has the best overall solution stability in the various plasticizers tested. A benzyl alcohol to OBPA weight ratio of about 2/1 also exhibited excellent stabi-lity in the solutions with lower OBPA levels. When the benzyl alcohol/OBPA weight ratio was about 1/1, solutions having lower levels (e.g. about 2%) of OBPA were more stable than those at higher levels. The data also indicates that high levels of silicone oil can cause unstable solutions, and, therefore, when this polymer processing aid is employed it should be used at low levels. Mineral spirits, while providing acceptable stability, would not be a preferred polymer processing aid where freeze-thaw stability is critical.

Compositions W-lA through W-45 from Table II were also subjected to heat stability tests by adding the composition to a poly (vinyl chloride) plastisol in an amount such that the resulting composition contained 5% by weight plasticizing composition, and forming a film from the resulting composition.
This film was then divided into several samples and placed in an oven at about 177C. Samples were then removed from the oven at five minute intervals for 40 minutes and examined for heat stability. All of the ~ilms tested were heat stable.

~;~95~7;2 A typical plasticizing composition according to this invention was tested to determine whether the aryl alkanol solvent contained therein had any adverse effect when the plasticizing composition is employed in a vinyl resin. The plasticizing composition was prepared by heating the following ingredients to about 160C.

PLASTICIZING COMPOSITION

INGREDIENTS WT %

OBPA 3.41 Benzyl alcohol 5.50 DI~P plasticizer 91.09 This plasticizing composition was incorporated into a typical plasticized poly ~vinyl chloride) dry blend formulation which contained the following.

PVC DRY BLEND FORMULATION
.

INGREDIENT AMOUNT (gms) PVC 1500.0 DOP plasticizer 600.0 Heat stabilizer 90.0 Stearic acid lubricant 3. 75 Total2,193.75 ~ms The plasticizing composition was used in an amount so that the OBPA was present in the PVC dry blend formulation at the recom-mended level of about 500 parts per million. The resulting PVC
dry blend containing the plasticizing composition was processed on a two-roll mill for approximateLy 15 minutes at about 163C.
During this time, the molten plastic was observed for heat stability, processing characteristics, excessive fuming of the benzyl alcohol, and irritation to the mill operator. No unusual processing difficulties, such as sticking to the miLl or failure to flux or form a sheet on the hot rollers, were observed. The formulation showed no signs of degradation or excessive fuming.

~;~95~7~
No irritation or odor was observed during processing. Thu-~, this example demonstrates that benzyl alcohol does not adversely affect the processing of typical pla~tic materials.

Antimicrobial efficacy was tested by preparing PVC films as described in Example 5 which contained a polymer processing aid-containing composition according to this invention which contained the following ingredients:
PLASTICIZING COMPOSITION
.

INGREDIENT WT ~

OBPA 3.41 ~enzyl alcohol 5.50 DIDP 91,09 A control was also made in like manner, except that it contain d no antimicrobial compound.
Round samples ~l inch diameter) were cut from the PVC film samples. These round samples were then placed on a glass plate or petri dish which was previously coated with agar, inoculated with the test microorganism, and placed in an incubator under con-ditions and for a period of time which would normally permit the microorganism to grow on untreated agar. The dish or plate was then removed and examined for growth of the microorganism on the PVC sample.
The results of the above tests are summarized below. The term "Zone of Inhibition" refers the width of an area (measured in millimeters) around t~e round PVC sample in which no microorganism growth occurred on the agar. The "Growth" or "Stain" observations refer to the presence of microorganism growth or stain on the round sample (also called the "contact area").

SAMPLE

With plasticizing R/NGCA
composition , 95i~7~2 Control 0/GCA

ZONE OF INHIBITION(mm)/GROWTH FOR R PNEUMON_AE

SAMPLE

With plasticizing 4/NGCA
composition Control 0/GCA

ZONE OF INHIBITION(mm)/STAIN FOR PINK STAIN

SAMPLE

Wlth plasticizing 6/NS
composition Control 0/HS

ZONE OF INHIBITION(mm)/GROWTH FOR MIXED FUNGAL_SPORE

SAMPLE

With plasticizing 15/NG
composition Control 0/TG

: NGCA=No Growth in Contact Area ÇCA=Growth in Contact Area NS-No Stain MS=Moderate Stain HS=Heavy Stain NG=No Growth TG=Trace Growth LG=Light Growth The above data shows that the polymer processing aid-contain-ing composition is effective in preventing the growth of microorganism9 on the PVC fi1m.

Claims (85)

1. A liquid microbiocidal solution comprising an aryl alkanol and a microbiocidal compound dissolved therein, said microbiocidal compound being selected from the group consisting of N-(2-methylnaphthyl) maleimide, isoindole dicarboximides having a sulfur atom bonded to the nitrogen atom of the dicarboximide group, isothiazolinone compounds, phenoxarsines and phenarsazines.

2. A microbiocidal solution according to claim 1 wherein the microbiocidal compound is selected from the group consisting of phenoxarsines and phenarsazines.

3. A microbiocidal solution according to claim 1 wherein the microbiocidal compound is selected from the group consisting of N-(2-methylnaphthyl) maleimide; bis-N-[(1,1,2,2,-tetrachloroethyl)thio]-4-cyclohexene-1,2-dicarboximide; N-trichloromethylthio phthalimide; and 2-(n-octyl-4-isothiazolin-3-one).

4. A microbiocidal solution according to claim 2 wherein the microbiocidal compound is selected from the group consisting of 10,10'-oxybisphenarsazine; 10, 10'-thiobisphenoxarsine; 10,10'-oxybisphenarsazine and 10, 10'-thiobisphenoxarsine.

5. A microbiocidal solution according to claim 4 wherein the microbiocidal compound is 10,10'-oxybisphenoxarsine.

6. A microbiocidal solution according to claim 4 wherein the aryl alkanol is benzyl alcohol, the microbiocidal compound is 10, 10'-oxybisphenoxarsine and the microbiocidal compound comprises about 25% by weight of the solution.

7. A composition comprising a plasticizer as a polymer processing aid and, in an amount at least sufficient to impart microbiocidal properties to the composition, a microbiocidal compound which is present in the composition as the solute in an aryl alkanol solvent, said microbiocidal compound being selected from the group consisting of N-(2-methylnaphthyl) maleimide, isoindole dicarboxamides having a sulfur atom bonded to the nitrogen atom of the dicarboximide group, isothiazolinone compounds, phenoxarsines and phenarsazines.

8. A composition according to claim 7 wherein the plasticizer is selected from the group consisting of di(2-ethyl hexyl) phthalate, diisodecyl phthalate, butyl benzyl phthalate and epoxidized soya bean oil.

9. A composition according to claim 7 wherein the microbiocidal compound is selected from the group consisting of N-(2-methylnaphthyl) maleimide, isoindole dicarboximides having a sulfur atom bonded to the nitrogen atom of the dicarboximide group, and isothiazolinone compounds.

10. A composition according to claim 7 wherein the microbiocidal compound is selected from the group consisting of phenoxarsines and phenarsazines.

11. A composition according to claim 9 wherein the microbiocidal compound is selected from the group consisting of N-(2-methylnaphthyl) maleimide; bis-N-[1,1,2,2-tetrachlorethyl) thio]-4-cyclohexene-1,2-dicarboximide; N-trichloromethylthio-4-cyclohexene-1,2-dicarboximide; N-trichloromethylthio phthalimide; and 2-(n-octyl-4-isothiazolin-3-one).

12. A composition according to claim 10 wherein the microbiocidal compound is selected from 10,10'-oxybisphenoxarsine; 10,10'-thiobisphenoxarsine; 10,10'-oxybisphenarsazine and 10, 10'-thiobisphenoxarsine.

13. A composition according to claim 12 wherein the microbiocidal compound is 10, 10'-oxybisphenoxarsine.

14. A composition according to claim 7 wherein the aryl alkanol is benzyl alcohol.

15. A composition according to claim 7 which comprises at least about 2% by weight, based on the total weight of the composition, of the microbiocidal compound.

16. A composition according to claim 7 which comprises at least about 5% by weight, based on the total weight of the composition, of the microbiocidal compound.

17. A composition according to claim 7 which comprises about 50 ppm to about 10,000 ppm microbiocidal compound.

18. A composition according to claim 7 wherein the microbiocidal compound is 10, 10'-oxybisphenoxarsine and the aryl alkanol is benzyl alcohol.

19. A composition according to claim 18 which comprises at least about 5% by weight, based on the total composition weight, of 10, 10'-oxybisphenoxarsine.

20. A composition according to claim 7 wherein the polymer processing aid is di(2-ethyl hexyl) phthalate, the microbiocidal compound is 10,10'-oxybisphenoxarsine, and the aryl alkanol solvent is benzyl alcohol.

21. A composition according to claim 7 wherein the weight ratio of aryl alkanol solvent to microbiocidal compound is from about 0.5/1 to about 5/1.

22. A composition according to claim 18 wherein the weight ratio of benzyl alcohol to 10,10'-oxybisphenoxarsine is from about 0.5/1 to about 5/1.

23. A composition according to claim 21 wherein the weight ratio of aryl alkanol solvent to microbiocidal compound is from about 1/1 to about 3/1.

24. A composition according to claim 7 which comprises about 1% to about 5% by weight, based on the total composition weight, of the microbiocidal compound, and the weight ratio of aryl alkanol solvent to microbiocidal compound is from about 0.5/1 to about 5/1.

25. A composition according to claim 21 which comprises at least about 2% by weight, based on the total weight of the composition, of the microbiocidal compound.

26. A composition according to claim 21 which comprises at least about 5% by weight, based on the total weight of the composition, of the microbiocidal compound.

27. A composition according to claim 21 which comprises from about 5% to about 20% by weight, based on the total weight of the composition, of the microbiocidal compound, said aryl alkanol solvent being present in an amount such that the weight ratio of the aryl alkanol solvent to microbiocidal compound is from about 3/1 to about 5/1.

28. A composition according to claim 27 wherein the microbiocidal compound is 10,10'-oxybisphenoxarsine and the aryl alkanol is benzyl alcohol.

29. A composition according to claim 7 which comprises about 2% by weight, based on the total weight of the composition, of 10,10'-oxybisphenoxarsine, said composition having a weight ratio of aryl alkanol solvent to 10,10'-oxybisphenoxarsine of about 4/1.

30. A composition according to claim 7 which comprises about 2% by weight, based on the total weight of the composition, of 10,10'-oxybisphenoxarsine, said composition having a weight ratio of aryl alkanol solvent to 10,10'-oxybisphenoxarsine of about 3/1.

31. A composition according to claim 7 which comprises about 2% by weight, based on the total weight of the composition, of 10,10'-oxybisphenoxarsine, said composition having a weight ratio of aryl alkanol solvent to 10,10'-oxybisphenoxarsine of about 1/1.

32. A composition according to claim 7 which comprises about 5% by weight, based on the total weight of the composition, of 10,10'-oxybisphenoxarsine, said composition having a weight ratio of aryl alkanol solvent to 10,10'-oxybisphenoxarsine of about 4/1.

33. A composition according to claim 7 which comprises about 5% by weight, based on the total weight of the composition, of 10,10'-oxybisphenoxarsine, said composition having a weight ratio of aryl alkanol solvent to 10,10'-oxybisphenoxarsine of about 3/1.

34. A composition according to claim 7 which comprises about 1% by weight, based on the total weight of the composition, of 10,10'-oxybisphenoxarsine, said composition having a weight ratio of aryl alkanol solvent to 10,10'-oxybisphenoxarsine of about 4/1.

35. A composition according to claim 7 which comprises about 1% by weight, based on the total weight of the composition, of 10,10'-oxybisphenoxarsine, said composition having a weight ratio of aryl alkanol solvent to 10,10'-oxybisphenoxarsine of about 3/1.

36. A composition according to claim 7 which comprises about 1% by weight, based on the total weight of the composition, of 10,10'-oxybisphenoxarsine, said composition having a weight ratio of aryl alkanol solvent to 10,10'-oxybisphenoxarsine of about 1/1.

37. A process for imparting microbiocidal properties to a polymer composition comprising adding to the polymer composition a liquid microbiocidal solution comprising an aryl alkanol and, in an amount sufficient to impart microbiocidal properties to the polymer composition, a microbiocidal compound dissolved in the aryl alkanol, the microbiocidal compound being selected from the group consisting of N-(2-methylnaphthyl) maleimide, isoindole dicarboximides having a sulfur atom bonded to the nitrogen atom of the dicarboximide group, isothiazolinone compounds, phenoxarsines and phenarsazines.

38. A process according to claim 37 wherein the amount of microbiocidal compound is about 50 ppm to about 10,000 ppm.

39. A process according to claim 37 wherein the microbiocidal compound is selected from the group consisting of phenoxarsines and phenarsazines.

40. A process according to claim 37 wherein the microbiocidal compound is selected from the group consisting of N-(2-methylnaphthyl) maleimide; bis-N-[(1,1,2,2-tetrachloroethyl)thio]-4-cyclohexene-1,2-dicarboximide; N-trichloromethylthio-4-cyclohexene-1,2-dicarboximide; N-trichloromethylthio phthalimide; and 2-(n-octyl-4-isothiazolin-3-one).

41. A process according to claim 39 wherein the microbiocidal compound is selected from 10,10'-oxybisphenoxarsine; 10,10'-thiobisphenoxarsine; 10,10'-oxybisphenarsazine and 10,10'-thiobisphenoxarsine.

42. A process according to claim 41 wherein the microbiocidal compound is 10,10'-oxybisphenoxarsine.

43. A process according to claim 37 wherein the aryl alkanol is benzyl alcohol.

44. A process according to claim 37 wherein the polymer is selected from the group consisting of polyolefins, vinyl resins and polyurethanes.

45. A process according to claim 44 wherein the polymer is a vinyl resin.

46. A process according to claim 37 wherein the aryl alkanol is benzyl alcohol and the microbiocidal compound is 10,10'-oxybisphenoxarsine.

47. A process according to claim 46 wherein the amount of 10,10'-oxybisphenoxarsine is about 50 ppm to about 10,000 ppm.

48. The product produced by the process of claim 37.

49. The product produced by the process of claim 38.

50. The product produced by the process of claim 39.

51. The product produced by the process of claim 40.

52. The product produced by the process of claim 41.

53. The product produced by the process of claim 42.

54. The product produced by the process of claim 43.

55. The product produced by the process of claim 44.

56. The product produced by the process of claim 45.

57. The product produced by the process of claim 46.

58. The product produced by the process of claim 47.

59. A process for imparting microbiocidal properties to a polymer composition comprising adding to the polymer composition a composition comprising a polymer processing aid and, in an amount at least sufficient to impart microbiocidal properties to the polymer composition, a microbiocidal compound which is present in the polymer processing aid as the solute in an aryl alkanol solvent, the microbiocidal compound selected from the group consisting of N-(2-methylnaphthyl) maleimide, isoindole dicarboximides having a sulfur atom bonded to the nitrogen atom of the dicarboximide group, isothiazolinone compounds, phenoxarsines and phenarsazines.

60. A process according to claim 59 wherein the polymer processing aid is selected from the group consisting of plasticizers and solvents.

61. A process according to claim 60 wherein the polymer processing aid is a plasticizer.

62. A process according to claim 61 wherein the plasticizer is selected from the group consisting of di(2-ethyl hexyl) phthalate,diisodecyl phthalate, butyl benzyl phthalate and epoxidized soya bean oil.

63. A process according to claim 59 wherein the amount of microbiocidal compound is about 50 ppm to about 10,000 ppm.

64. A process according to claim 59 wherein the microbiocidal compound is selected from the group consisting of N-(2-methylnaphthyl) maleimide, isoindole dicarboximides having a sulfur atom bonded to the nitrogen atom of the dicarboximide group, and isothiazolinone compounds.

65. A process according to claim 59 wherein the microbiocidal compound is selected from the group consisting of phenoxarsines and phenarsazines.

66. A process according to claim 64 wherein the microbiocidal compound is selected from the group consisting of N-(2-methylnaphthyl) maleimide; bis-N-[(1,1,2,2-tetrachloroethyl)thio]-4-cyclohexene-1,2-dicarboximide; N-trichloromethylthio-4-cyclohexene-1,2-dicarboximide; N-trichloromethylthio phthalimide; and 2-(n-octyl-4-4-isothiazolin-3-one).

67. A process according to claim 65 wherein the microbiocidal compound is selected from 10,10'-oxybisphenoxarsine; 10,10'-thiobisphenoxarsine; 10,10'-oxybisphenarsazine and 10, 10'-thiobisphenoxarsine.

68. A process according to claim 67 wherein the microbiocidal compound is 10,10'-oxybisphenoxarsine.

69. A process according to claim 59 wherein the aryl alkanol is benzyl alcohol.

70. A process according to claim 59 wherein the polymer processing aid is a plasticizer, the microbiocidal compound is 10,10'-oxybisphenoxarsine and the aryl alkanol is benzyl alcohol.

71. A process according to claim 59 wherein the aryl alkanol solvent is present in an amount such that the weight ratio of aryl alkanol solvent to microbiocidal compound is from about 0.5/1 to about 5/1.

72. A process according to claim 71 wherein the weight ratio of aryl alkanol solvent to microbiocidal compound is about 0.5/1 to about 3/1.

73. The product produced by the process of claim 59.

74. The product produced by the process of claim 60.

75. The product produced by the process of claim 61.

76. The product produced by the process of claim 62.

77. The product produced by the process of claim 63.

78. The product produced by the process of claim 65.

79. The product produced by the process of claim 66.

80. The product produced by the process of claim 67.

81. The product produced by the process of claim 68.

82. The product produced by the process of claim 69.

83. The product produced by the process of claim 70.

84. The product produced by the process of claim 71.

85. The product produced by the process of claim 72.